Note the upper-lip freckle
To me, “Win” is the most forward looking song on Young Americans. It points the way toward Station To Station in style in bitter, cold, contemptuous irony. The soul sound of the rest of the record is beginning to mutate into something bleak.
What is it about? It is a difficult song to draw concrete meaning from. There is much unsaid and much complexity in what is said. The chorus line of “All you have to do is win” is utterly bitter. This is coming from a man who has—by nearly every standard—”won” at life. He his a famous rock star, the world is at his feet, and all dust, nothing but ashes in his mouth. But, “seems you’re not suppose to lose,” so he keeps trying, though he’s not even sure why anymore.